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Pineapple Upside Down Cupcakes

When you can pick up a sweet treat and eat it with your hands you have found the pot of gold. These pineapple upside down cupcakes are delish.

There’s nothing quite like a tasty treat that is portable to make it all the more fun and exciting. These pineapple upside down cake cupcakes are easy to make and even easier to eat!

Try out this fun recipe for the summer today!

When you can pick up a sweet treat and eat it with your hands you have found the pot of gold. These pineapple upside down cupcakes are delish.

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Cupcakes are all the rage!  These baby cakes are being served everywhere. You can find them on the dessert table at family meals or even at weddings.

It doesn’t surprise me that people love cupcakes. When you can pick up a sweet treat and eat it with your hands you have found the pot of gold. 

And these pineapple upside down cupcakes are delicious. Pineapple Upside Down Cupcakes have become my husband’s new favorite dessert.

I’m a chocolate loving kind of girl, but can definitely eat my way through a few Pineapple Upside Down Cupcakes when the opportunity presents itself.

You will need a few simple ingredients to get you started:

Yellow Cake Mix (eggs, oil, water) Whatever your particular mix calls for


Brown Sugar

Crushed Pineapple

Maraschino Cherries 

Something to grease your cupcake tins with. (I use Crisco, but a good non-stick spray should work, too)

You will also need to have some wax paper on hand so you can invert the cupcakes onto the wax paper when releasing them. 

Pineapple Upside Down Cupcakes

Here are a few tips to make this recipe work better:

When mixing these cupcakes if your cake mix calls for the water you will be replacing it with the pineapple juice you drained from the can. If you don’t have enough juice just add water until you get to the right measurements.

Be sure your cupcake tins are well greased. This will prevent sticking. 

When you add the butter, brown sugar pineapple and cherry push it down with the back of a spoon so it’s an even layer. 

Put these on the middle oven rack. 

If you are using a dark pan reduce your cooking temperature by 25 degrees. 

Let the cupcakes cool for 5 mins before inverting them. 

Following those few tips will ensure that these cupcakes will be a new family favorite if you can keep them around long enough for everyone to try! 

Curious minds want to know, Do you eat the cherry on top of your pineapple upside down cake?

I do not! If it was a chocolate covered cherry I’d probably eat it. But it’s a big no on maraschino cherries for me!

If you’re interested in a savory cupcake, be sure to try out these Maple Bacon Cupcakes next!

Printable Pineapple Upside Down Cake Cupcakes Recipe:

Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes

Yield: 24
Prep Time: 15 minutes
Cook Time: 25 minutes
Total Time: 40 minutes

These easy pineapple upside down cake cupcakes are sure to be a hit. They're delcious, adorable, and portable!


  • 1/2 cup butter, melted
  • 1 1/2 cups brown sugar
  • 24 maraschino cherries
  • 20 ounce can crushed pineapple drained
  • 1 box of your favorite yellow cake mix
  • 3 eggs
  • 1/3 cup oil
  • 1 1/3 cup pineapple juice


  1. Move an oven rack into the middle of the oven. Preheat oven to 350 degrees F.
  2. Grease 24 muffin cups. (Try using shortening or a good non-stick spray)
  3. Line a work surface with waxed paper
  4. Spoon 1 teaspoon melted butter into the bottom of each muffin cup.
  5. Spoon 1 tablespoon brown sugar in each muffin cup.
  6. Press a maraschino cherry into the center of the brown sugar in each muffin cup.
  7. Spoon a heaping tablespoon of crushed pineapple over the cherry and compact it with the back of a spoon into an even layer.
  8. Mix yellow cake mix as directed adding in your oil, eggs, etc.. replacing the water with pineapple juice until moistened, about 30 seconds. Turn mixer speed to medium and mix for 2 minutes.
  9. Pour cake batter into the muffin cup, filling them almost to the top; do not overfill.
  10. Bake in the preheated oven until a toothpick inserted into the center of a cupcake comes out clean, about 20 minutes.
  11. Allow cupcakes to cool at least 5 minutes before inverting muffin cups onto the wax paper to release. Serve with pineapple and cherry sides up.


The oil and eggs are listed in the ingredients because every yellow cake mix I have ever used calls for those ingredients in those measurements. You may have to adjsut the ingredients accordingly depending on the cake mix you use.

Crushed pineapple works best.

Nutrition Information
Yield 24 Serving Size 1
Amount Per Serving Calories 225Total Fat 8gSaturated Fat 3gTrans Fat 0gUnsaturated Fat 4gCholesterol 33mgSodium 202mgCarbohydrates 37gFiber 1gSugar 27gProtein 2g

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  1. What size muffin tins? Large where there are 6 on a tray or regular where there are 12 on a tray?

  2. I’ve been making them for years ~ My fiancé’ calls them PUDcakes. I usually dice up the cherries so that you get a small bit of it in each bite.

  3. Mine stuck also. Used non stick pan and spray but they stuck pretty bad. They are not pretty like yours but taste great! I will lower my oven temp next time to see if that helps.


    Just made them, have a problem with them sticking to the wax paper (I used parchment paper thinking it won’t stick) but it did stick. Did I take them out of the muffin tin too soon. They look delicious and hubby said they taste delicious. So that’s good. Left them in muffin tin little over 5 min about 6 or so. Lots of the brown sugar & pineapple stuck in tin also, used butter knife to spread on cupcakes. I did get 24 cupcakes so that’s really good. Just want to know about the sticking to the paper issues. Thanks

    1. I normally use the non-stick or silicone muffin pans and grease them with non-stick spray so I don’t see much sticking in the pan. (Maybe lower your oven temp 25 degrees) I’ve also never had them stick to the wax paper. Maybe non-stick spray on your parchment may help. Thanks

  5. I have been making Pineapple UpSide Down Cupcakes for several years. I always use a Pineapple Supreme Cake Mix I drain my can of pineapple and use that juice for the liquid requested to make the cake mix. Most always have enough juice but if not I just add water to the juice. Big hit when I take them to a function.

  6. Can they be made ahead of time and eaten the next day or should they be eaten fresh out of the oven and warm?

    1. We always make them ahead of time. I’ve never tried them warm, but we just may have too. Thanks!

  7. I can’t eat butter or margarine. Is there some other type of oil that would work?

    1. Sorry I haven’t tried this recipe in any alternate forms. Let me know if you have any ideas. Thanks!

  8. Great tasting treat. I did notice though that the printable recipe does not say to drain the crushed pineapple. Glad I double checked.
    Keep up the great work.

  9. When it says muffin cups , does that mean straight into the pan or into muffin papers?

  10. Hi! I’m one of the co-hosts from the Welcome Home Wednesdays Link Up. These cupcakes sound delicious! I am a huge fan of pineapple upside down cake but never thought of putting them in a cupcake. These are perfect for a summer cookout. Thank you for sharing.

  11. These look absolutely delicious!!! A mini version on my favorite cake!! Thanks for sharing can’t wait to try!!

  12. These cupcakes look so yummy! Thanks for sharing your tasty recipe with us this week on the Monday Funday Party!

  13. These are so much fun! The perfect Easter dessert to bring to the big family dinner. Thanks for sharing your recipe with us at Merry Monday this week!

  14. Stephanie Lett says:

    I just made these mini upside down pineapple cakes, if you could smell my house as they were baking !!!! So easy to make and quick . I am adding these tomorrow to my Thanksgiving desert table.